EP2292449B1 - Luftreifen - Google Patents

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Publication number
EP2292449B1
EP2292449B1 EP10175013A EP10175013A EP2292449B1 EP 2292449 B1 EP2292449 B1 EP 2292449B1 EP 10175013 A EP10175013 A EP 10175013A EP 10175013 A EP10175013 A EP 10175013A EP 2292449 B1 EP2292449 B1 EP 2292449B1
Authority
EP
European Patent Office
Prior art keywords
tire
rubber
phr
previous
methylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
Application number
EP10175013A
Other languages
English (en)
French (fr)
Other versions
EP2292449A1 (de
Inventor
Erik Paul Sandstrom
Paul Harry Sandstrom
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Goodyear Tire and Rubber Co
Original Assignee
Goodyear Tire and Rubber Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co
Publication of EP2292449A1 publication Critical patent/EP2292449A1/de
Application granted granted Critical
Publication of EP2292449B1 publication Critical patent/EP2292449B1/de
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34922—Melamine; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/372—Sulfides, e.g. R-(S)x-R'
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C9/00—Reinforcements or ply arrangement of pneumatic tyres
    • B60C9/0007—Reinforcements made of metallic elements, e.g. cords, yarns, filaments or fibres made from metal
    • B60C2009/0021—Coating rubbers for steel cords

Definitions

  • a tire is a composite of several components each serving a specific and unique function yet all synergistically functioning to produce the desired performance.
  • an in-situ resin is included in a rubber composition to impart desirable properties to the rubber composition, including hardness, tear strength, and adhesion to reinforcement.
  • methylene acceptor-methylene donor systems are used as in-situ resins. Performance and safety requirements place an ever increasing demand for improved rubber compounds. Therefore, there exists a need for improved rubber compositions particularly for use in wire-reinforced tire applications, such as tire beads.
  • EP-A- 0 629 652 describes a laminate of rubber and steel cord wherein the rubber comprises a diene based elastomer and dithiodipropionic acid.
  • EP-A- 0 943 466 describes a tire with a sidewall carcass reinforcement comprising at least one diene-based elastomer and at least one of dithiodipropionic acid, benzoic acid and salicylic acid.
  • US-A- 4,513,123 describes a sulfur-curable rubber skim stock which exhibits improved adhesion to brass-plated steel.
  • the rubber skim stock comprises diene-based elastomers and a small amount of dithiodipropionic acid.
  • the present invention is directed to a pneumatic tire having a wire-reinforced component according to claim 1.
  • the present invention relates to a pneumatic tire.
  • Pneumatic tire means a laminated mechanical device of generally toroidal shape (usually an open torus) having beads and a tread and made of rubber, chemicals, fabric and steel or other materials.
  • the present invention relates to both bias and radial-ply tires.
  • the present invention is a radial-ply tire.
  • Radial-ply tire means a belted or circumferentially-restricted pneumatic tire in which the carcass ply cords which extend from bead to bead are laid at cord angles between 65° and 90° with respect to the equatorial plane of the tire.
  • the rubber composition comprises salicylic acid. In one embodiment, the rubber composition includes from 2 to 20 phr of salicylic acid. In one embodiment, the rubber composition includes from 3 to 15 phr of salicylic acid.
  • the rubber composition for use in the tire component preferably contains a natural or synthetic diene based elastomer or rubber.
  • the rubbers include medium vinyl polybutadiene, styrene-butadiene rubber, synthetic cis-1,4-polyisoprene, synthetic 3,4-polyisoprene, natural rubber, cis-polybutadiene, styrene-isoprene rubber, styrene-isoprene-butadiene rubber, acrylonitrile-butadiene rubber, carboxylated acrylonitrile-butadiene rubber and mixtures thereof.
  • the rubber is natural rubber, styrene-butadiene rubber or cis-polybutadiene.
  • the component of the tire of the present invention may further contain an in-situ resin that is the reaction product of a methylene acceptor and a methylene donor.
  • In-situ resins are formed in the rubber stock and involve the reaction of a methylene acceptor and a combination methylene donor.
  • methylene donor is intended to mean a chemical capable of reacting with a methylene acceptor and generate the resin in-situ.
  • Examples of methylene donors which are suitable for use in the present invention include hexamethylene tetramine and N-substituted oxymethylmelamines, of the general formula: wherein X is hydrogen or an alkyl having from 1 to 8 carbon atoms, R 1' R 2 , R 3 , R 4 and R 5 are individually selected from the group consisting of hydrogen, an alkyl having from 1 to 8 carbon atoms, the group -CH 2 OX or their condensation products.
  • Specific methylene donors include hexakis-(methoxymethyl)melamine, N,N',N"-trimethyl/N,N',N"-trimethylolmelamine, hexamethylolmelamine, N,N',N"-dimethylolmelamine, N-methylolmelamine, N,N'-dimethylolmelamine, N,N',N"-tris(methoxymethyl)melamine, N,N'N"-tributyl-N,N',N"-trimethylol-melamine, hexamethoxymethylmelamine, and hexaethoxymethylmelamine.
  • the N-methylol derivatives of melamine are prepared by known methods.
  • the amount of methylene donor in the rubber stock may vary. In one embodiment, the amount of additional methylene donor ranges from 0.5 to 4 phr. In another embodiment, the amount of additional methylene donor ranges from 1 to 3 phr.
  • methylene acceptor is known to those skilled in the art and is used to describe the reactant to which the methylene donor reacts to form what is believed to be a methylol monomer.
  • the condensation of the methylol monomer by the formation of a methylene bridge produces the resin.
  • the initial reaction that contributes the moiety that later forms into the methylene bridge is the methylene donor wherein the other reactant is the methylene acceptor.
  • Representative compounds which may be used as a methylene acceptor include but are not limited to resorcinol, resorcinolic derivatives, monohydric phenols and their derivatives, dihydric phenols and their derivatives, polyhydric phenols and their derivatives, unmodified phenol novolak resins, modified phenol novolak resin, resorcinol novolak resins and mixtures thereof.
  • methylene acceptors include those disclosed in US-B- 6,605,670 ; US-B- 6,541,551 ; US-B- 6,472,457 ; US-B- 5,945,500 ; US-B- 5,936,056 ; US-B- 5,688,871 ; US-B- 5,665,799 ; US-B- 5,504,127 ; US-B-5,405,897 ; US-B- 5,244,725 ; US-B- 5,206,289 ; US-B- 5,194,513 ; US-B- 5,030,692 ; US-B-4,889,481 ; US-B- 4,605,696 ; US-B- 4,436,853 ; and US-B- 4,092,455 .
  • modified phenol novolak resins include but are not limited to cashew nut oil modified phenol novolak resin, tall oil modified phenol novolak resin and alkyl modified phenol novolak resin.
  • the methylene acceptor is resorcinol.
  • methylene acceptors include activated phenols by ring substitution and a cashew nut oil modified novalak-type phenolic resin.
  • activated phenols by ring substitution include resorcinol, cresols, t-butyl phenols, isopropyl phenols, ethyl phenols and mixtures thereof.
  • Cashew nut oil modified novolak-type phenolic resins are commercially available from Schenectady Chemicals Inc under the designation SP6700. The modification rate of oil based on total novolak-type phenolic resin may range from 10 to 50 percent.
  • various processes may be used for production of the novolak-type phenolic resin modified with cashew nut oil.
  • phenols such as phenol, cresol and resorcinol may be reacted with aldehydes such as formaldehyde, paraformaldehyde and benzaldehyde using acid catalysts.
  • acid catalysts include oxalic acid, hydrochloric acid, sulfuric acid and p-toluenesulfonic acid. After the catalytic reaction, the resin is modified with the oil.
  • the amount of methylene acceptor in the rubber stock may vary. In one embodiment, the amount of methylene acceptor ranges from 0.5 to 5 phr. In another embodiment, the amount of methylene acceptor ranges from 1 to 3 phr.
  • the rubber compositions used in tire components would be compounded by methods generally known in the rubber compounding art, such as mixing the various sulfur-vulcanizable constituent rubbers with various commonly used additive materials such as, for example, curing aids, such as sulfur, activators, retarders and accelerators, processing additives, such as oils, resins including tackifying resins, silicas, and plasticizers, fillers, pigments, fatty acid, zinc oxide, waxes, antioxidants and antiozonants, peptizing agents and reinforcing materials such as, for example, carbon black.
  • curing aids such as sulfur, activators, retarders and accelerators
  • processing additives such as oils, resins including tackifying resins, silicas, and plasticizers
  • fillers pigments, fatty acid, zinc oxide, waxes, antioxidants and antiozonants
  • peptizing agents and reinforcing materials such as, for example, carbon black.
  • the additives mentioned above are selected and commonly used in conventional amounts.
  • the rubber compound may contain various conventional rubber additives.
  • the addition of carbon black comprises about 20 to 200 parts by weight of diene rubber (phr). In another embodiment, from about 50 to about 100 phr of carbon black is used.
  • carbon blacks may be used. Included in the list of carbon blacks are those known under the ASTM designations N299, N315, N326, N330, M332, N339, N343, N347, N351, N358, N375, N539, N550 and N582.
  • processing aids may be present and can include, for example, aromatic, naphthenic, and/or paraffinic processing oils.
  • Silica if used, may be used in an amount of about 5 to about 80 phr, often with a silica coupling agent.
  • Representative silicas may be, for example, hydrated amorphous silicas.
  • Typical amounts of antioxidants comprise about 1 to about 5 phr.
  • Representative antioxidants may be, for example, diphenyl-p-phenylenediamine, polymerized 1,2-dihydro-2,2,4-trimethylquinoline and others, such as, for example, those disclosed in the Vanderbilt Rubber Handbook (1990), Pages 343 through 362 .
  • Typical amounts of antiozonants comprise 1 to 5 phr.
  • Representative antiozonants may be, for example, those disclosed in the Vanderbilt Rubber Handbook (1990), Pages 363 through 367 .
  • Typical amounts of fatty acids, if used, which can include stearic acid comprise 0.5 to 3 phr.
  • Typical amounts of zinc oxide comprise 1 to 10 phr.
  • Typical amounts of waxes comprise 1 to 5 phr. Often microcrystalline waxes are used.
  • Typical amounts of peptizers comprise 0.1 to 1 phr.
  • Typical peptizers may be, for example, pentachlorothiophenol and dibenzamidodiphenyl disulfide. The presence and relative amounts of the above additives are considered to be not an aspect of the present invention which is more primarily directed to the utilization of the combination of the reaction product of the methylene acceptor and combination methylene donor.
  • the vulcanization is conducted in the presence of a sulfur vulcanizing agent.
  • suitable sulfur vulcanizing agents include elemental sulfur (free sulfur) or sulfur donating vulcanizing agents, for example, an amine disulfide, polymeric polysulfide or sulfur olefin adducts.
  • the sulfur vulcanizing agent is elemental sulfur.
  • sulfur vulcanizing agents are used in an amount ranging from 0.5 to 8 phr. In another embodiment 3 to 5 phr of sulfur vulcanizing agents are used.
  • Accelerators are used to control the time and/or temperature required for vulcanization and to improve the properties of the vulcanizate.
  • a single accelerator system may be used, i.e., primary accelerator.
  • a primary accelerator is used in amounts ranging from 0.5 to 2.5 phr.
  • combinations of two or more accelerators may be used, including a primary accelerator which is generally used in the larger amount (0.5 to 2.0 phr), and a secondary accelerator which is generally used in smaller amounts (0.05 to 0.50 phr) in order to activate and to improve the properties of the vulcanizate.
  • delayed action accelerators may be used which are not affected by normal processing temperatures but produce satisfactory cures at ordinary vulcanization temperatures.
  • Suitable types of accelerators that may be used in the present invention are amines, disulfides, guanidines, thioureas, thiazoles, thiurams, sulfenamides, dithiocarbamates and xanthates.
  • the primary accelerator is a sulfenamide.
  • the secondary accelerator may be a guanidine, dithiocarbamate or thiuram compound.
  • the rubber compound may contain any of the cobalt materials known in the art to further promote the adhesion of rubber to metal.
  • cobalt materials which may be employed include cobalt salts of fatty acids such as stearic, palmitic, oleic, linoleic and the like; cobalt salts of aliphatic or alicyclic carboxylic acids having from 6 to 30 carbon atoms, such as cobalt neodecanoate; cobalt chloride, cobalt naphthenate; cobalt carboxylate and an organo-cobalt-boron complex commercially available under the designation Manobond C from Wyrough and Loser, Inc, Trenton, New Jersey. Manobond C is believed to have the structure: in which R 6 is an alkyl group having from 9 to 12 carbon atoms.
  • Amounts of cobalt compound which may be employed depend upon the specific nature of the cobalt material selected, particularly the amount of cobalt metal present in the compound.
  • the amount of the cobalt material may range from about 0.2 to 5 phr. In another embodiment, the amount of cobalt compound may range from about 0.5 to 3 phr. In one embodiment, the amount of cobalt material present in the stock composition is sufficient to provide from about 0.01 percent to about 0.50 percent by weight of cobalt metal based upon total weight of the rubber stock composition. In another embodiment, the amount of cobalt material present in the stock composition is sufficient to provide from about 0.03 percent to about 0.2 percent by weight of cobalt metal based on total weight of wire coat composition.
  • the metallic wire or cord used according to the present invention may be steel, zinc-plated steel or brass-plated steel.
  • the metallic cord is brass plated steel.
  • the steel substrate may be derived from those known to those skilled in the art.
  • the steel used for wire may be conventional tire cord rod including AISI grades 1070, 1080, 1090 and 1095.
  • the steel may additionally contain varying levels of carbon and microalloying elements such as Cr, B, Ni and Co.
  • cord means one or more of a reinforcing element, formed by one or more filaments or wires which may or may not be twisted or otherwise formed. Therefore, cords using the present invention may comprise from one (monofilament) to multiple filaments.
  • the number of total filaments or wires in the cord may range from 1 to 134. Preferably, the number of filaments or wires per cord ranges from 1 to 49.
  • the wire or cord may be used in a belt structure, bead or carcass of a tire.
  • Belt structure means at least two layers of plies of parallel cords, underlying the tread, unanchored to the bead and having both left and right cord angles in the range from about 17 to about 27 degrees with respect to the equatorial plane (EP) of the tire.
  • Carcass means the tire structure apart from the belt structure, the tread and the undertread but including the beads. The carcass ply includes reinforcing cords embedded in an elastomeric substance and that these components are considered to be a single entry.
  • Bead means that part of the tire comprising an annular tensile member wrapped by the carcass ply and shaped, with or without other reinforcement elements such as flippers, chippers, apexes, toe guards, and chafers, to fit the design rim.
  • the tire can be built, shaped, molded and cured by various methods which will be readily apparent to those having skill in such art.
  • the prepared tire of this invention is conventionally shaped and cured by methods known to those having skill in such art.
  • Cure properties were determined using a Monsanto oscillating disc rheometer (MDR).
  • MDR Monsanto oscillating disc rheometer
  • a description of oscillating disc rheometers can be found in the Vanderbilt Rubber Handbook edited by Robert O. Ohm (Norwalk, Conn., R. T. Vanderbilt Company, Inc., 1990), Pages 554 through 557 .
  • the use of this cure meter and standardized values read from the curve are specified in ASTM D-2084.
  • a typical cure curve obtained on an oscillating disc rheometer is shown on Page 555 of the 1990 edition of The Vanderbilt Rubber Handbook .
  • Standard bead wire adhesion tests were conducted by embedding a single brass-plated cord in the respective rubber compositions. The rubber articles were then cured as indicated. The wire in these rubber compositions were then subjected to a pull-out test, according to ASTM Standard ASTM D1871 Method 1. The results of these pull-out tests (SBAT) and percent rubber coverage (%RC) are given below and expressed in Newtons. Table 1 Sample No. 1 1 * 2* 3 4 * 5* 6 7 Resorcinol 0 2.5 2.5 2.5 2.5 0 0 0 M.A.
  • Sample 5 containing dithiopropionic acid showed significantly higher adhesion at 95oC for both original and aged samples as compared to control Sample 1.
  • Sample 6 containing a combination of salicylic acid and dithiopropionic acid showed significantly higher adhesion both original and aged samples at both 23oC and 95oC, compared to control sample 1.

Claims (13)

  1. Luftreifen mit einem drahtverstärkten Bauteil, wobei das Bauteil umfasst:
    (A) einen Metalldraht; und
    (B) eine Kautschukzusammensetzung, die ein dienbasiertes Elastomer und 1 bis 20 ThK Salicylsäure umfasst;
    wobei die Kautschukzusammensetzung mit dem Draht in Kontakt ist.
  2. Reifen nach Anspruch 1, wobei besagtes dienbasiertes Elastomer einen Bestandteil umfasst, ausgewählt aus der aus Polybutadien mit mittlerem Vinylgehalt, Styrol-Butadien-Kautschuk, synthetischem cis-1,4-Polyisopren, synthetischem 3,4-Polyisopren, Naturkautschuk, cis-Polybutadien, Styrol-Isopren-Kautschuk, Styrol-Isopren-Butadien-Kautschuk, Acrylnitril-Butadien-Kautschuk, carboxyliertem Acrylnitril-Butadien-Kautschuk und Mischungen davon bestehenden Gruppe.
  3. Reifen nach mindestens einem der vorgenannten Ansprüche, weiter ein in situ-Harz umfassend, das einen Methylendonator und einen Methylenakzeptor umfasst.
  4. Reifen nach Anspruch 3, wobei der Methylendonator einen Bestandteil umfasst, ausgewählt aus der aus Hexamethylentetramin, Hexakis-(methoxymethyl)melamin, N,N',N"-Trimethyl/N,N',N"-Trimethylolmelamin, Hexamethylolmelamin, N,N',N"-Dimethylolmelamin, N-Methylolmelamin, N,N'-Dimethylolmelamin, N,N',N"-Tris(methoxymethyl)melamin, N,N',N"-Tributyl-N,N',N"-trimethylolmelamin, Hexamethoxymethylmelamin und Hexaethoxymethylmelamin bestehenden Gruppe.
  5. Reifen nach Anspruch 4, wobei der Methylendonator Hexamethoxymethylmelamin umfasst.
  6. Reifen nach Anspruch 4, wobei der Methylendonator Hexamethylentetramin umfasst.
  7. Reifen nach mindestens einem der vorgenannten Ansprüche, wobei die Menge an Methylendonator sich auf 0,5 bis 4 ThK beläuft.
  8. Reifen nach mindestens einem der vorgenannten Ansprüche, wobei der Methylenakzeptor einen Bestandteil umfasst, ausgewählt aus der aus Resorcinol, Resorcinolderivaten, einwertigen Phenolen und deren Derivaten, zweiwertigen Phenolen und deren Derivaten, mehrwertigen Phenolen und deren Derivaten, unmodifizierten Phenol-Novolakharzen, modifiziertem Phenol-Novolakharz, Resorcinol-Novolakharzen und Mischungen davon bestehenden Gruppe.
  9. Reifen nach Anspruch 8, wobei der Methylenakzeptor Resorcinol umfasst.
  10. Reifen nach mindestens einem der vorgenannten Ansprüche, wobei die Kautschukzusammensetzung 2 bis 9 ThK Salicylsäure umfasst.
  11. Reifen nach mindestens einem der vorgenannten Ansprüche, wobei die Kautschukzusammensetzung 3 bis 6 ThK Salicylsäure umfasst.
  12. Reifen nach mindestens einem der vorgenannten Ansprüche, wobei das Kautschukbauteil ein Drahtüberzug ist.
  13. Reifen nach mindestens einem der vorgenannten Ansprüche, wobei das drahtverstärkte Kautschukbauteil ein Wulst ist.
EP10175013A 2009-09-03 2010-09-02 Luftreifen Not-in-force EP2292449B1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12/553,384 US8053510B2 (en) 2009-09-03 2009-09-03 Pneumatic tire

Publications (2)

Publication Number Publication Date
EP2292449A1 EP2292449A1 (de) 2011-03-09
EP2292449B1 true EP2292449B1 (de) 2012-05-09

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP10175013A Not-in-force EP2292449B1 (de) 2009-09-03 2010-09-02 Luftreifen

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US (1) US8053510B2 (de)
EP (1) EP2292449B1 (de)
AT (1) ATE556872T1 (de)

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JP6292118B2 (ja) * 2012-12-17 2018-03-14 横浜ゴム株式会社 積層体、タイヤ用インナーライナー及び空気入りタイヤ
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Publication number Publication date
EP2292449A1 (de) 2011-03-09
US20110054109A1 (en) 2011-03-03
US8053510B2 (en) 2011-11-08
ATE556872T1 (de) 2012-05-15

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